Vacation rentals in Westport Island

4.99 out of 5 average rating, 135 reviews

A modern outdoor sauna, designed with a circular wooden structure, is illuminated from within. Its glass door opens to reveal a warm interior with seating and soft lighting, surrounded by a snowy landscape and tall trees in the evening light.

Cabin in Georgetown

Sauna+Near Beach+Pond+Outdoor Shower+FirePit+A/C

Come relax at Pine Cabin, one of two cabins on 8 acres with a pond minutes from one of the best beaches in Maine. Unwind in your private outdoor cedar glass sauna w/forest views & refresh in our seasonal outside shower! * Minutes to Reid State Park & 5 Island🦞 * Fire Pit * Family Own & Run * Gas Grill * Private Bedroom w/Queen Bed * Loft w/Queen Bed & Record Player * Rain Shower * Custom cabinets & couch * Screen porch * AC/Heat * EV charger * Fast Wifi * Beach Gear * Smart TV * Generator

4.94 out of 5 average rating, 141 reviews

William Larrabee House

Stylish, spacious 1 bedroom apartment with separate entrance. On 2nd floor, 1 flight up. Air conditioning in the bedroom only. 1.5 blocks from the Kennebec River, a short walk to downtown Bath, Saturday farmers' market and restaurants... a 20 minute drive to some of Maine's most stunning beaches. Just 15 minutes to Brunswick, 20 minutes to Freeport and 45 minutes to downtown Portland. A perfect base for college visits (Bates and Bowdoin), overnight travel breaks, or exploring the midcoast!

4.93 out of 5 average rating, 123 reviews

A wine glass filled with rosé sits on a wooden table. In the background, trees provide a natural frame, and a view of gentle hills and a pond can be seen, creating a serene outdoor setting.

Home in Boothbay Harbor

Renovated home with amazing waterfront views

Welcome to Dancing Pines Cottage! We are located across from West Harbor Pond with beautiful water views in each room. Relax on the deck or bbq on the patio or take a short drive into charming Boothbay Harbor town for lobster rolls. We have three bedrooms and a den/office and 2 full bathrooms and can accommodate up to 7 guests. The house is private and has ample parking. One week rentals for June, July, and August (Saturday-Saturday). Starting January 2025 we will no longer allow pets.

4.91 out of 5 average rating, 336 reviews

A deer stands gracefully on a green lawn, framed by vibrant foliage. Wooden garden beds can be seen in the background, adding a touch of rustic charm to the natural setting. The image captures a serene moment in the woods, highlighting the area’s wildlife.

Loft in Edgecomb

Cozy Loft in the Woods (Dogs Welcome)

Bright, cozy loft, surrounded by deep woods, a tranquil retreat offering true peace, separate from our home, w/ its own entrance; we're here if needed. Located between Boothbay, Damariscotta, & Wiscasset, 1 mile from Route 1 and 27, on 13 acres, abutting 100s of acres of preserve land - provides the best of both worlds - woods rich with abundant birds, but less than 15 minutes from restaurants, shops & activities, plus, dedicated WiFi /2 Smart TVs. Dogs welcome, no cats due to allergies.

Farm stay in Westport Island

The rustic exterior of the historic retreat features a weathered brown shingle facade and a vibrant red front door. A spacious deck extends towards the water, surrounded by greenery and providing a serene view of the tidal Sheepscot River at sunset.

4.83 out of 5 average rating, 126 reviews

The Stilt House

Once the island Trading Post (in the 1820's) now serves as a private retreat on Westport Island. The whole property has been listed on the National Register of Historic Places since 1982. The building is nestled at the water's edge, half on land and half on stilts over the tidal waters of the Sheepscot River. The property has its own private deck, island, rocky beach, trails and hammock. This is an old structure - over 200 years old! A great piece of history and an absolute oasis.

Cottage in Boothbay Harbor

A quaint cottage is seen at dusk, with warm light glowing from the windows. A pathway made of stepping stones leads toward the entrance, bordered by lush greenery and soft landscaping. Tall trees provide a natural frame, complementing the inviting ambiance.

4.98 out of 5 average rating, 415 reviews

The Cottage at the McCobb House

Freshly renovated inside and out, the cottage is your private Maine camp. Located on an acre and a half of wooded grounds, and surrounded by forest, the cottage feels secluded, but it’s only a mile to the restaurants, shops, and waterfront attractions of bustling Boothbay Harbor. With hiking trails in the Pine Tree Preserve that adjoins the property and the Lobster Cove Meadow Preserve a five minute walk up the road, you can also explore nature and enjoy the solitude of the woods.

4.91 out of 5 average rating, 116 reviews

An airy cabin interior features wood beams and a large sliding glass door, providing access to a deck and surrounding greenery. A small dining area with a table and two chairs is visible alongside a well-equipped kitchen area, complete with modern appliances.

Tiny home in Bowdoinham

Sweet Fern Cabin on Merrymeeting Bay

Nestled in the woods on 2.5 waterfront acres where the Muddy River meets Merrymeeting Bay. The cabin is 350 square feet of simple living with a panoramic view. There is a three season hot water outdoor shower and wood burning stove with plenty of wood included. Kitchen is fully stocked with cooking supplies and has off grid cold water sink. Outbuilding with composting toilet is right out the back door. Kayaks and stand up paddle board are available to rent for an additional fee.

A small gravel patio features a glass-top table surrounded by two black folding chairs. The setting is bordered by lush greenery and colorful flowers, creating a private outdoor seating area.

4.97 out of 5 average rating, 101 reviews

1820s Maine Cottage with Garden

Enjoy your stay in a cozy, shipbuilder's cottage in Bath, Maine. This quaint apartment attached to a family home has its own private entrance and contains one bedroom, one bathroom, a full kitchen, and a living room with antique details that reflect its 200-year old history. Only a 15-minute walk to historic downtown Bath, a 3-minute drive to Thorne Head Preserve, and a 25-minute drive to Reid State Park and Popham Beach. Come appreciate everything MidCoast Maine has to offer!

Guest suite in Phippsburg

5 out of 5 average rating, 111 reviews

Suite 19 min to Popham, 10 min to Bath

Our two story in-law suite is relatively new. This one bedroom is perfect for a family or a quiet romantic retreat. Located on 8 acres of very private pristine Maine landscape. 10 minutes to Bath. 19 minutes to Popham beach. 30 minutes to Freeport. 45 minutes to Portland. 5 minutes to public boat launch. Unfortunately, as much as we love furry family members, due to health risks for our family we are not able to host animals including service dogs. ❤️ 🐶 🐈‍⬛ 💕

4.92 out of 5 average rating, 210 reviews

A wooden deck is featured with two traditional adirondack chairs, positioned invitingly beside the entrance. Surrounding greenery and trees provide a natural backdrop, enhancing the outdoor space's peaceful atmosphere.

Guest suite in Woolwich

Private Guest Apartment with separate entrance.

Your perfect base for discovering all the wonderful places Midcoast Maine has to offer. Located on a peaceful wooded lot, this one bedroom apartment sits on the ground floor of our 2-story home. Separate private deck entry with parking. sitting room with a dining table that looks out onto the deck, queen bedroom, private bathroom with jetted tub and separate shower, fully equipped kitchenette; NEW FURNACE-quiet and efficient.

4.95 out of 5 average rating, 133 reviews

A spacious wooden deck is featured, complete with a white swing and a picnic table. Natural surroundings are visible, including trees in the background. Sunlight is observed casting shadows across the deck, enhancing the inviting outdoor space.

Guest suite in Boothbay

Linekin Guest Suite

Tucked away guest studio attached to main home that you will have all to yourself with basic amenities and a sky lighted bathroom. A few minutes to Ocean Point and hiking trails and less than 10 minutes to Boothbay Harbor. **Please note there are stairs that need to be climbed on the front deck in order to access the property. Use the directions provided as your GPS sometimes puts you in a circle around Boothbay!

4.99 out of 5 average rating, 219 reviews

A crisp bathroom features a modern vanity with a rectangular mirror above a sink. Built-in shelving holds decorative items. A toilet is positioned beside the door, which opens to a view of the living area with natural light filtering through.

Guest suite in Bath

Bath Historic District Apartment

Located in the Bath historic district, this one bedroom apartment is located just a few blocks from downtown. The apartment has a queen bed in the bedroom and also a queen sleeper sofa in the living room. The home was built in the late 1700's, but with the recent upgrades, it now feels fresh with classic elements. Located in Midcoast Maine, this apartment is an quick drive to the beach, hiking trails and museums.

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Popular amenities for Westport Island vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Westport Island

Superhost

A cozy living area is highlighted by large windows that invite natural light. A comfortable sofa and a lounge chair are positioned around a rustic coffee table. A propane stove is situated in the corner, complemented by a view of the outdoor deck.

Cottage in Edgecomb

4.8 out of 5 average rating, 44 reviews

River View Casita

MariaRating, 5 stars7 months ago

Cottage was in a perfect location and very private and peaceful. Driving distance to a lot of nice towns and restaurants. Cottage was quaint, clean and had all the essentials. I loved the PDF they supplied before the visit with very clear instructions for check in, check out and parking. They had a ton of recommendations for things to do and places to eat at! We will be back!

Superhost

A charming street scene depicts a historic downtown area illuminated by streetlights at dusk. Flags adorn buildings and shops, while parked cars are lined along the wide street. A prominent clock tower is visible in the background, contributing to the area's inviting atmosphere.

4.82 out of 5 average rating, 38 reviews

Bright Studio Apt in Historic District Home

SamanthaRating, 5 stars3 weeks ago

Great stay! We took a weekend trip up to coastal Maine and this was a great place to stay for a long weekend. Not far from Brunswick, Boothbay, Freeport, Portland — great location!

4.98 out of 5 average rating, 42 reviews

A sandy beach stretches out under a cloudy sky, with gentle waves lapping at the shore. A rocky outcrop is visible in the distance, surrounded by a line of trees. Footprints mark the sand, leading towards the horizon.

Cottage in Georgetown

Serene Coveside Cottage

DanielRating, 5 stars2 weeks ago

My wife and I stayed at Viktor's place for our honeymoon. As soon as we walked through the door it felt like we were in a second home. We loved using the projector and home theater setup to play Nintendo Switch and watch Netflix. I liked that the bedroom had its own separate A/C unit from the living room. Made it so much easier to set the temperature during the day and evening. The combined washer/dryer unit worked great and didn't have any issues drying our clothes. Nearly every morning we were greeted by neighboring deer who came to feed on the backyard grass. The surrounding area (Georgetown, Bath, and Boothbay Harbor) are really great to find good food, parks, and entertainment nearby. I highly recommend this place. It really is a gem in the middle of the forest.

A compact kitchen features stainless steel appliances, including a refrigerator and microwave. A coffee maker and assorted condiments are arranged neatly on the countertop. Decorative shelving displays plants and dishware, while patterned flooring adds visual interest to the space.

4.99 out of 5 average rating, 80 reviews

Wabi Sabi

NorahRating, 5 stars2 weeks ago

This was our 2nd stay at Wabi Sabi. The location can’t be beat! It’s great for seeing Bath but also going up or down the coast. There is a flight of steep stairs to get up to the place, so if you have an issue with stairs, this isn’t the place for you. We at OystHers twice and at Mae’s for breakfast. Our favorite lobster dock is Five Islands about 20 minutes south. Had a great time and will be back!

4.9 out of 5 average rating, 91 reviews

The entrance to the A-Frame features warm wooden paneling and a circular sign with a colorful design. Large glass doors lead into the interior, framed by dark wood, with trees visible in the background.

Tiny home in Wiscasset

Tiny A-Frame Romantic Getaway

AbbygayleRating, 5 stars2 weeks ago

The perfect one-night getaway from the grind. The cedar hot tub was a godsend and David was very helpful and communicative! Great location and value!!

Superhost

An outdoor deck features a rectangular table surrounded by several chairs, shaded by a large umbrella. A flagpole displays an American flag, while the serene waterfront view is framed by trees and open green space, reflecting clear skies dotted with clouds.

Home in Wiscasset

5 out of 5 average rating, 3 reviews

Seahorse Shores of Wiscasset, ME

BrettRating, 5 stars9 months ago

Great location on Back River. short drive to wiscasset and groceries. Fun to sit and watch the tides.

5 out of 5 average rating, 45 reviews

A view of a peaceful street in Bath, Maine, features red brick buildings lined with small shops and banners. The historic town hall, with a prominent dome, is illuminated by an orange and pink sunset sky, creating a warm backdrop against the architecture.

Home in Bath

The Cottage

VictorRating, 5 stars2 weeks ago

Jody and Matt were great hosts. The space they have created is so cozy and spacious. I can't say enough about how helpful the guide they created was. The local recommendations they had listed were super helpful and made our stay more special with some of the places we had visited.